EP0335115B1 - Pharmazeutische und kosmetische Zusammensetzungen auf der Basis von Benzoylperoxid und quaternären Ammoniumsalzen - Google Patents

Pharmazeutische und kosmetische Zusammensetzungen auf der Basis von Benzoylperoxid und quaternären Ammoniumsalzen Download PDF

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Publication number
EP0335115B1
EP0335115B1 EP89103375A EP89103375A EP0335115B1 EP 0335115 B1 EP0335115 B1 EP 0335115B1 EP 89103375 A EP89103375 A EP 89103375A EP 89103375 A EP89103375 A EP 89103375A EP 0335115 B1 EP0335115 B1 EP 0335115B1
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Prior art keywords
composition according
denotes
quaternary ammonium
composition
radical
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Expired - Lifetime
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EP89103375A
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English (en)
French (fr)
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EP0335115A2 (de
EP0335115A3 (en
Inventor
Henri Sebag
Irina Beck
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LOreal SA
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LOreal SA
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/38—Percompounds, e.g. peracids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders

Definitions

  • the present invention relates to pharmaceutical and cosmetic compositions based on benzoyl peroxide and quaternary ammonium salts and their use, especially for the treatment of acne.
  • the etiopathology of acne although poorly defined, originates in the formation of a characteristic lesion: the comedo. This results from obstruction of the pilosebaceous canal as a result of dyskeratinization of the infundibulum zone of the canal. The main effect of the obstruction is hyperproliferation of the resident skin strains, which then triggers an inflammatory reaction of the body.
  • benzoyl peroxide has proved for many years to be a particularly interesting keratolytic agent, further having good bacteriostatic properties.
  • benzoyl peroxide was then combined with the antibiotics.
  • the latter has, in particular, been associated with erythromycin (FR-A-2378523).
  • antibiotics associated or not with benzoyl peroxide have the major disadvantage during prolonged use, to make the bacterial flora resistant. They become less active during subsequent treatments. (LEYDEN JJ, J. Am Acad Dermatol 8 (1) 41-45 (1983)).
  • Stable detergent compositions possibly used for the cleaning of the bit, which can contain simultaneously a quaternary ammonium surfactant such as benzalkonium chloride, cetalkonium chloride, cetylpyridinium chloride, benzethonium chloride or cethexonium bromide and benzoyl peroxide (FR-A-2328039).
  • a quaternary ammonium surfactant such as benzalkonium chloride, cetalkonium chloride, cetylpyridinium chloride, benzethonium chloride or cethexonium bromide and benzoyl peroxide (FR-A-2328039).
  • the Applicant has just discovered, quite surprisingly, that it is possible to obtain stable compositions in the treatment of acne, cutaneous ulcer, and generally in the treatment of dermatoses and skin disorders. , by associating benzoyl peroxide with certain quaternary ammonium derivatives.
  • benzoyl peroxide can be used at low doses, with the advantage of improving skin tolerance.
  • compositions according to the invention are well tolerated by the body. They have very good antibacterial properties, without inducing resistance of strains, they are keratolytic, bacteriostatic, especially vis-à-vis Propionibacterium Acnes which is one of the main germs responsible for acne and are active in treatment and reduction of the number of comedones.
  • compositions according to the invention are suitable for the treatment of cutaneous disorders and dermatoses, such as, in particular, acne and cutaneous ulcer.
  • the present invention therefore relates to a topical pharmaceutical and / or cosmetic composition containing benzoyl peroxide and at least one quaternary ammonium salt such as those described below.
  • the invention also relates to a cosmetic treatment method implementing such an association.
  • composition intended for a topical application in accordance with the invention is essentially characterized in that it contains, in a physiologically acceptable medium, benzoyl peroxide and a quaternary ammonium salt chosen from alkyl sulphates or sulphonates, aryl sulphonates and quaternary ammonium alkyl aryl sulfonates.
  • X ⁇ denotes an alkyl sulphate or sulphonate anion, aryl sulphonate or alkyl aryl sulphonate.
  • Particularly preferred anions are chosen from the anions of the following formulas:
  • compositions may be in the form of solutions, emulsions, suspensions, gels or dispersions, containing at least one compound corresponding to formula (I) in concentrations of between 0.01 and 25% by weight, relative to the total weight of the composition and preferably between 0.1 and 5% by weight and benzoyl peroxide in concentrations of between 0.1 and 20% by weight relative to the total weight of the composition and preferably included between 0.5 and 10% by weight.
  • compositions in accordance with the invention may also contain foaming or emulsifying surfactants, polymers such as cellulose and its derivatives, guar gum, heterobiopolysaccharides, polyacrylic acids and their derivatives, poly- ⁇ -alanine, ethers or esters of polyethylene glycols, colloidal silica, superfatting agents, emollients, wetting agents, pH regulators, penetration agents, preservatives, sunscreens, perfumes, dyes and / or pigments having as their function of coloring the skin or the composition itself and any other ingredient usually used in compositions intended for topical application.
  • foaming or emulsifying surfactants polymers such as cellulose and its derivatives, guar gum, heterobiopolysaccharides, polyacrylic acids and their derivatives, poly- ⁇ -alanine, ethers or esters of polyethylene glycols, colloidal silica, superfatting agents, emollients, wetting agents, pH regulators, penetration agents, preservatives
  • the galenic forms mainly conditioned for the topical route are especially in the form of solutions, creams, milks, gels, dispersions or microemulsions more or less thickened, soaked swabs, ointments, sticks or in the form of soap bars.
  • Another subject of the invention is therefore also constituted by the use of pharmaceutical compositions for the preparation of a medicament for the treatment of dermatoses, such as, in particular, acne, cutaneous ulcers, warts and dyskeratinizations of the skin. skin.
  • dermatoses such as, in particular, acne, cutaneous ulcers, warts and dyskeratinizations of the skin. skin.
  • compositions in accordance with the invention, may be used for the cosmetic treatment of the skin, especially as a cleaning and disinfecting, comedolytic, keratolytic product.
  • Another object of the invention relates to a cosmetic treatment process characterized in that it consists in applying to the skin a composition according to the invention for purifying or purifying the latter.
  • This composition is used as a skin cream once or twice a day for one to twelve weeks.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (18)

1. Zusammensetzung zur topischen Anwendung, dadurch gekennzeichnet, dass sie in einem physiologisch akzeptablen Milieu Benzoylperoxid und ein quartäres Ammoniumsalz umfasst, ausgewählt aus den quartären Ammoniumsalzen von Alkylsulfaten oder -sulfonaten, Arylsulfonaten und den Alkylarylsulfonaten.
2. Zusammensetzung nach Anspruch 1, dadurch gekennzeichnet, dass das quartäre Ammoniumsalz durch die folgende allgemeine Formel (I) dargestellt ist:
Figure imgb0012
 worin bedeuten:
(i) R₁ eine Gruppe R-[OC₂H₃Z] n -[OCH₂-CHOH-CH₂] p ―
Figure imgb0013
worin bedeuten:
0 ≦ n ≦ 6 und p bedeutet 0 oder 1;
R bedeutet ein Alkylradikal, ein Alkylcycloalkylradikal oder Alkylarylradikal mit 8 bis 32 C-Atomen, wobei die aliphatische Kette gegebenenfalls durch eine Ether-, Amid-, Sulfonamid- oder Carbamatgruppe unterbrochen sein kann und/oder einen Hydrokylsubstituenten tragen kann;
wenn n von 0 unterschiedlich ist, bedeutet Z H, CH₃ oder CH₂OH;
wenn Z H oder CH₃ bedeutet, ist p gleich 0;
wenn Z CH₂OH bedeutet, ist p gleich 1;
die Gruppe (OC₂H₃Z) kann die eine oder die andere der nachfolgenden Verknüpfungen aufweisen:
Figure imgb0014
(ii) R₂ bedeutet ein C₁₋₂₂-Alkylradikal, welches gegebenenfalls eine oder mehrere Hydrokylgruppen umfassen kann;
(iii) R₃ bedeutet ein C₁₋₆-Alkylradikal, ein C₁₋₆-Monohydrokyalkylradikal, ein C₃₋₆-Polyhydrokyalkylradikal oder ein Benzylradikal;
(iv) R₄ bedeutet ein Alkyl- oder Alkyloxyradikal mit 1 bis 18 C-Atomen;
(v) R₂ und R₃ können zusammen mit dem Stickstoffatom einen Heterozyklus, wie das Piperidin oder Morpholin bilden; oder
(vi) R₁, R₂ und R₃ können mit dem Stickstoffatom einen Pyridin-, Methylpyridin- oder Hydrokypyridinring bilden;
X⁻ bedeutet ein Alkylsulfat- oder -sulfonat-, Arylsulfonat- oder Alkylarylsulfonat-anion.
3. Zusammensetzung nach Anspruch 2, dadurch gekennzeichnet, dass das Anion X⁻ aus den Gruppen mit den folgenden Formeln ausgewählt ist:
CH₃OSO₃⁻, C₂H₅OSO₃⁻, CH₃SO₃⁻,
Figure imgb0015
Figure imgb0016
 oder
Figure imgb0017
4. Zusammensetzung nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass das quartäre Ammoniumsalz, welches durch die allgemeine Formel (I) dargestellt ist, ausgewählt ist aus Trimethyl-laurylammonium, Dimethyl-hydroxyethyl-cetylammonium, Dimethyl-methoxy-laurylammonium, Trimethyl-laurylamido-propylammonium, Cetylpyridinium, Cetyloxypyridinium, Dimethyl-benzyl-cetylammonium, Dimethyl-benzyl-octylphenory-ethoxyethylammonium, Dimethyl-hydroxycyclohexyl-cetylammonium, N-Methyl-, N-Cetylimidazolium- oder Methyllauryl-morpholinium.
5. Zusammensetzung nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass das Benzoylperoxid in einer Menge von 0,1 bis 20 Gew.%, bezogen auf das Gesamtgewicht der Zusammensetzung, vorhanden ist.
6. Zusammensetzung nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass das quartäre Ammoniumsalz der allgemeinen Formel (I) in einer Menge von 0,01 bis 25 Gew.%, bezogen auf das Gesamtgewicht der Zusammensetzung, vorhanden ist.
7. Zusammensetzung nach Anspruch 5, dadurch gekennzeichnet, dass das Benzoylperoxid in einer Menge von 0,5 bis 10 Gew.%, bezogen auf das Gesamtgewicht der Zusammensetzung, vorhanden ist.
8. Zusammensetzung nach Anspruch 6, dadurch gekennzeichnet, dass das quartäre Ammoniumsalz der allgemeinen Formel (I) in einer Menge von 0,1 bis 5 Gew.%, bezogen auf das Gesamtgewicht der Zusammensetzung, vorhanden ist.
9. Zusammensetzung nach einem der Ansprüche 1 bis 8 zur Anwendung als Medikament, dadurch gekennzeichnet, dass der geeignete Träger ein pharmazeutisch akzeptabler Träger ist.
10. Zusammensetzung nach einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, dass der geeignete Träger ein kosmetisch akzeptabler Träger ist.
11. Zusammensetzung nach einem der Ansprüche 1 bis 10, dadurch gekennzeichnet, dass sie in Form von Gelen, Lösungen, Dispersionen, Emulsionen oder Suspensionen vorliegt.
12. Zusammensetzung nach einem der Ansprüche 1 bis 11, dadurch gekennzeichnet, dass sie in Form einer Creme, einer Milch, eines Gels, eines imprägnierten Tupfers, einer Pommade, eines Stiftes oder in Form eines Stückes Seife vorhanden ist.
13. Zusammensetzung nach einem der Ansprüche 1 bis 12, dadurch gekennzeichnet, dass sie zusätzlich zumindest ein anderes Anti-Aknemittel enthält.
14. Zusammensetzung nach einem der Ansprüche 1 bis 13, dadurch gekennzeichnet, dass sie zusätzlich zumindest einen Sonnenfilter enthält.
15. Verwendung der Zusammensetzungen nach Anspruch 9 zur Herstellung eines Medikamentes zur Behandlung von Dermatosen.
16. Verwendung der Zusammensetzungen nach Anspruch 15 zur Behandlung von ulzeröser Haut, von Warzen und Dyskeratose der Haut.
17. Verwendung der Zusammensetzungen nach Anspruch 9 zur Herstellung eines Medikamentes zur Behandlung von Akne.
18. Verfahren zur kosmetischen Behandlung, gekennzeichnet durch Auftragung einer Zusammensetzung, wie sie in Anspruch 10 definiert ist, auf die Haut, um die Haut zu reinigen und zu säubern.
EP89103375A 1988-03-09 1989-02-27 Pharmazeutische und kosmetische Zusammensetzungen auf der Basis von Benzoylperoxid und quaternären Ammoniumsalzen Expired - Lifetime EP0335115B1 (de)

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Application Number Priority Date Filing Date Title
AT89103375T ATE69162T1 (de) 1988-03-09 1989-02-27 Pharmazeutische und kosmetische zusammensetzungen auf der basis von benzoylperoxid und quaternaeren ammoniumsalzen.

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FR8803042A FR2628319B1 (fr) 1988-03-09 1988-03-09 Compositions pharmaceutiques et cosmetiques a base de peroxyde de benzoyle et de sels d'ammonium quaternaires
FR8803042 1988-03-09

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EP0335115A2 EP0335115A2 (de) 1989-10-04
EP0335115A3 EP0335115A3 (en) 1989-10-18
EP0335115B1 true EP0335115B1 (de) 1991-11-06

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US (1) US4960772A (de)
EP (1) EP0335115B1 (de)
JP (1) JP2689991B2 (de)
AT (1) ATE69162T1 (de)
CA (1) CA1339085C (de)
DE (1) DE68900402D1 (de)
FR (1) FR2628319B1 (de)

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Publication number Publication date
FR2628319B1 (fr) 1990-12-07
JPH01268632A (ja) 1989-10-26
DE68900402D1 (de) 1991-12-12
US4960772A (en) 1990-10-02
FR2628319A1 (fr) 1989-09-15
EP0335115A2 (de) 1989-10-04
ATE69162T1 (de) 1991-11-15
EP0335115A3 (en) 1989-10-18
CA1339085C (fr) 1997-07-29
JP2689991B2 (ja) 1997-12-10

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